1. Field of the Invention
Two naturally occurring cyclopropenoid acids, sterculic and malvalic, comprise approximately 61% of the seed oils of Sterculia foetida, and are also present in lesser amounts in the seed oils of Hisbiscus syriacus, Lavatera trimestris, and Brachychiton populneum. In sterculia oil the cyclopropenoid distribution is about 54% sterculic and 7% malvalic, while in the other seed oils, malvalic predominates. These acids have also been reported in minor amounts in the leaf oils of two Malva species and at levels of up to about 3% in cottonseed oil. When cottonseed oil is incorporated into the diet of laying hens, it often causes a pinkish discoloration of the egg whites as well as an increased level of chick mortality. Prior interest in these compounds has therefore been primarily directed to elimination of the cyclopropenoid functionality. However, pending the development of a feasible conversion procedure, these compounds have commercial potential as a source of conjugated dienes and saturated branched chain fatty acids. Such compounds are useful in the production of plastics, coatings, lubricants, soaps, cosmetics, and other industrial and consumer products as summarized for example by Kinsman [JAOCS 56(11): 823A-827A (1979)]. This invention relates to a novel process for the catalytic rearrangement of these and other cyclopropenoid compounds to conjugated dienes and additionally to a catalytic hydrogenation for converting the dienes to their saturated branched chain counterparts.